Taylor Swift Picks Diddy As Her Ideal Prom Date In Resurfaced Clip

Sean “Diddy” Combs’ September arrest has caused internet users to dig deep and find old clips of celebrities speaking about the Bad Boy founder, and a lot of the sentiments have not aged the best. The most recent video that is making its rounds after resurfacing is from 2011, when Taylor Swift made an appearance on The Rachel Ray Show and picked Diddy as one of her ideal prom dates.

On the episode, the pop sensation was playing a rapid fire-style game and had to pick what fellow celebrities she would have taken to prom at the time. “It would be a group, and it would be a really fun group,” Swift said as she picked up pictures of Combs, Jennifer Lopez, Katy Perry, Justin Timberlake, and Sheryl Crow.

“Boy, you’re going on a freaky prom date,” Ray replied. Watch the moment below, which occurs around the 19-minute mark.

When the host asked Swift, who was 21 at the time, why she chose the people she did, Taylor replied, “Diddy’s really always been very nice to me.”

Ray added, “He’s a gentleman, isn’t he? He’s a lovely gentleman.”

“He would be fun to be in the prom group,” the 1989 singer said.

As the “I Need A Girl” rapper’s legal troubles continue to intensify, more clips of his past interviews are resurfacing and gaining traction after now being viewed in a different light. Another old moment that is being highlighted is Diddy’s November 2017 appearance on Martha Stewart and Snoop Dogg‘s VH1 cooking show, where he revealed what his “last words” would be.

In the clip of the show, titled Martha & Snoop’s Potluck Dinner Party, the two hosts are seen playing a card game with their guests that consisted of various open-ended prompts. The Bad Boy founder reads, “When I die, I want my last words to be?” and swiftly answers “I did it.” As he looks around the room, people laugh and clap, seemingly taking his response as a lighthearted joke.

On Sept. 16, 2024, the Love Album creator was arrested in NYC and charged with racketeering conspiracy; sex trafficking by force, fraud, or coercion; and transportation to engage in prostitution. Disturbing details from the court documents accused Diddy of using his companies to fund and facilitate “Freak Offs,” where he’d allegedly drug his victims and put them in sexually abusive situations. He is currently being held at the Metropolitan Detention Center in Brooklyn after being denied bail.